In the summer of 1999, he joined Piacenza along with Stefano Morrone and Flavio Roma as part of Simone Inzaghi's deal.
On 26 June 2002, he was bought back by Piacenza but on 29 June (one day before the end of 2001–02 fiscal year) left for Roma along with "team-mate" Davide Bagnacani, for Roma's Primavera youth team keeper Simone Paoletti and forward Alfredo Vitolo,[1] in another co-ownership deal for a total cost €4.5M.
[5] On 30 October 2007, Roma was fined €60,000 by Criminal Court of Rome for irregularity on youth player transfers.
After Di Fiordo was bought back by Piacenza in June 2003, he was signed by Rimini in co-ownership deal in July.
After Benevento won Serie C2 champion, he left for Lega Pro Seconda Divisione (ex-Serie C2) side Cisco Roma[9] which he became the regular starter.